Literature DB >> 21201019

Dichlorido(6-methyl-2,2'-bipyridine-κN,N')zinc(II).

Roya Ahmadi, Khadijeh Kalateh, Amin Ebadi, Vahid Amani, Hamid Reza Khavasi.

Abstract

In the mol-ecule of the title compound, [ZnCl(2)(C(11)n class="Species">H(10)N(2))], the Zn(II) atom is four-coordinated in a distorted tetra-hedral configuration by two N atoms from the 6-methyl-2,2'-bipyridine ligand and by two Cl atoms. There are π-π contacts between the pyridine ring and the five-membered ring, and also between the pyridine rings, [centroid-centroid distances = 3.685 (3) and 3.757 (3) Å, respectively].

Entities: Chemical Disease Species

Year: 2008 PMID： 21201019 PMCID： PMC2959229 DOI： 10.1107/S1600536808028894

Source DB: PubMed Journal: Acta Crystallogr Sect E Struct Rep Online ISSN： 1600-5368

Related literature

For related literature, see: Ahmadi et al. (2008 ▶); Yousefi et al. (2008 ▶); Khan & Tuck (1984 ▶); Gruia et al. (2007 ▶); Kozhevnikov et al. (2006 ▶); Reimann et al. (1966 ▶); Preston & Kennard (1969 ▶); Liu et al. (2004 ▶); Khavasi et al. (2008 ▶); Khalighi et al. (2008 ▶); Steffen & Palenik (1976 ▶, 1977 ▶); Qin et al. (1999 ▶); Lundberg (1966 ▶).

Experimental

Crystal data

[ZnCl2(C11n class="Species">H10N2)] M = 306.50 Monoclinic, a = 7.4674 (15) Å b = 9.5105 (17) Å c = 17.656 (4) Å β = 96.551 (18)° V = 1245.7 (4) Å3 Z = 4 Mo Kα radiation μ = 2.37 mm−1 T = 298 (2) K 0.30 × 0.15 × 0.10 mm

Data collection

Bruker SMART CCD area-detector diffractometer Absorption correction: multi-scan (SADABS; Sheldrick, 1998 ▶) T min = 0.668, T max = 0.802 10401 measured reflections 3358 independent reflections 2576 reflections with I > 2σ(I) R int = 0.078

Refinement

R[F 2 > 2σ(F 2)] = 0.060 wR(F 2) = 0.130 S = 1.17 3358 reflections 145 parameters H-atom parameters constrained Δρmax = 1.04 e Å−3 Δρmin = −0.70 e Å−3 Data collection: SMART (Bruker, 1998 ▶); cell refinement: SAINT (Bruker, 1998 ▶); data reduction: SAIn class="Chemical">NT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶). Crystal structure: contains datablocks I. DOI: 10.1107/S1600536808028894/hk2529sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536808028894/hk2529Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report

[ZnCl₂(C₁₁H₁₀N₂)]	F(000) = 616
M_r = 306.50	D_x = 1.634 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 1987 reflections
a = 7.4674 (15) Å	θ = 2.3–29.2°
b = 9.5105 (17) Å	µ = 2.37 mm⁻¹
c = 17.656 (4) Å	T = 298 K
β = 96.551 (18)°	Block, colorless
V = 1245.7 (4) Å³	0.30 × 0.15 × 0.10 mm
Z = 4

Bruker SMART CCD area-detector diffractometer	3358 independent reflections
Radiation source: fine-focus sealed tube	2576 reflections with I > 2σ(I)
graphite	R_int = 0.078
φ and ω scans	θ_max = 29.2°, θ_min = 2.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 1998)	h = −10→10
T_min = 0.668, T_max = 0.802	k = −12→13
10401 measured reflections	l = −24→24

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.060	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.130	H-atom parameters constrained
S = 1.17	w = 1/[σ²(F_o²) + (0.0315P)² + 1.9318P] where P = (F_o² + 2F_c²)/3
3358 reflections	(Δ/σ)_max = 0.004
145 parameters	Δρ_max = 1.05 e Å⁻³
0 restraints	Δρ_min = −0.70 e Å⁻³

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

	x	y	z	U_iso*/U_eq
Zn1	0.26730 (7)	0.26879 (5)	0.08829 (3)	0.04730 (16)
Cl1	0.53626 (17)	0.30874 (16)	0.15251 (8)	0.0708 (4)
Cl2	0.04386 (18)	0.40228 (15)	0.11668 (9)	0.0701 (4)
N1	0.2881 (5)	0.2367 (4)	−0.0261 (2)	0.0494 (8)
N2	0.2225 (5)	0.0559 (4)	0.0820 (2)	0.0460 (8)
C1	0.3141 (7)	0.3363 (6)	−0.0782 (3)	0.0619 (12)
H1	0.3145	0.4304	−0.0639	0.074*
C2	0.3400 (8)	0.3028 (7)	−0.1517 (3)	0.0741 (16)
H2	0.3573	0.3733	−0.1867	0.089*
C3	0.3401 (8)	0.1653 (7)	−0.1730 (3)	0.0726 (16)
H3	0.3590	0.1414	−0.2226	0.087*
C4	0.3121 (6)	0.0608 (6)	−0.1210 (3)	0.0626 (13)
H4	0.3120	−0.0335	−0.1350	0.075*
C5	0.2840 (5)	0.1004 (5)	−0.0466 (2)	0.0465 (9)
C6	0.2434 (5)	−0.0003 (5)	0.0127 (3)	0.0469 (9)
C7	0.2248 (7)	−0.1435 (5)	0.0005 (3)	0.0606 (12)
H7	0.2412	−0.1824	−0.0465	0.073*
C8	0.1819 (7)	−0.2268 (6)	0.0589 (4)	0.0698 (15)
H8	0.1668	−0.3230	0.0512	0.084*
C9	0.1608 (7)	−0.1700 (6)	0.1293 (4)	0.0679 (14)
H9	0.1323	−0.2268	0.1692	0.082*
C10	0.1834 (6)	−0.0254 (5)	0.1392 (3)	0.0566 (11)
C11	0.1652 (11)	0.0450 (7)	0.2132 (3)	0.091 (2)
H11A	0.0699	0.1132	0.2063	0.109*
H11B	0.2763	0.0912	0.2311	0.109*
H11C	0.1376	−0.0239	0.2498	0.109*

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Zn1	0.0498 (3)	0.0446 (3)	0.0483 (3)	−0.0009 (2)	0.0092 (2)	−0.0117 (2)
Cl1	0.0512 (6)	0.0826 (9)	0.0770 (9)	0.0013 (6)	0.0008 (6)	−0.0358 (7)
Cl2	0.0599 (7)	0.0712 (8)	0.0801 (9)	0.0137 (6)	0.0111 (6)	−0.0207 (7)
N1	0.0449 (18)	0.056 (2)	0.0475 (19)	0.0037 (16)	0.0055 (15)	−0.0037 (17)
N2	0.0411 (18)	0.0465 (18)	0.050 (2)	−0.0016 (14)	0.0053 (15)	−0.0024 (15)
C1	0.060 (3)	0.068 (3)	0.059 (3)	0.005 (2)	0.012 (2)	0.007 (2)
C2	0.078 (4)	0.096 (5)	0.051 (3)	0.004 (3)	0.015 (3)	0.010 (3)
C3	0.068 (3)	0.107 (5)	0.044 (3)	0.010 (3)	0.011 (2)	−0.004 (3)
C4	0.052 (3)	0.077 (3)	0.056 (3)	0.014 (2)	−0.001 (2)	−0.023 (3)
C5	0.0370 (19)	0.058 (2)	0.043 (2)	0.0091 (18)	−0.0018 (16)	−0.0112 (18)
C6	0.0346 (19)	0.048 (2)	0.056 (2)	0.0026 (17)	−0.0032 (17)	−0.0144 (19)
C7	0.057 (3)	0.049 (3)	0.074 (3)	0.001 (2)	0.004 (2)	−0.014 (2)
C8	0.058 (3)	0.043 (2)	0.106 (4)	0.000 (2)	0.001 (3)	−0.009 (3)
C9	0.057 (3)	0.058 (3)	0.088 (4)	−0.003 (2)	0.003 (3)	0.022 (3)
C10	0.050 (2)	0.060 (3)	0.059 (3)	0.002 (2)	0.003 (2)	0.002 (2)
C11	0.129 (6)	0.093 (5)	0.053 (3)	−0.010 (4)	0.025 (4)	0.013 (3)

Zn1—N1	2.066 (4)	C5—C6	1.475 (7)
Zn1—N2	2.053 (4)	C6—N2	1.360 (5)
Zn1—Cl1	2.2236 (15)	C6—C7	1.384 (6)
Zn1—Cl2	2.1995 (13)	C7—C8	1.367 (8)
C1—N1	1.350 (6)	C7—H7	0.9300
C1—C2	1.371 (7)	C8—C9	1.381 (8)
C1—H1	0.9300	C8—H8	0.9300
C2—C3	1.361 (9)	C9—C10	1.394 (7)
C2—H2	0.9300	C9—H9	0.9300
C3—C4	1.385 (8)	C10—N2	1.329 (6)
C3—H3	0.9300	C10—C11	1.488 (8)
C4—C5	1.406 (6)	C11—H11A	0.9600
C4—H4	0.9300	C11—H11B	0.9600
C5—N1	1.345 (6)	C11—H11C	0.9600

N1—Zn1—Cl1	111.08 (11)	N1—C5—C4	120.5 (5)
N2—Zn1—Cl1	109.16 (11)	N1—C5—C6	115.8 (4)
Cl2—Zn1—Cl1	116.72 (5)	C4—C5—C6	123.7 (4)
N1—Zn1—Cl2	116.84 (11)	N2—C6—C7	120.5 (5)
N2—Zn1—Cl2	117.28 (10)	N2—C6—C5	115.9 (4)
N2—Zn1—N1	80.31 (15)	C7—C6—C5	123.6 (4)
C1—N1—Zn1	126.6 (3)	C8—C7—C6	118.7 (5)
C5—N1—Zn1	113.8 (3)	C8—C7—H7	120.6
C5—N1—C1	119.6 (4)	C6—C7—H7	120.6
C6—N2—Zn1	113.6 (3)	C7—C8—C9	120.9 (5)
C10—N2—Zn1	125.5 (3)	C7—C8—H8	119.5
C10—N2—C6	120.8 (4)	C9—C8—H8	119.5
N1—C1—C2	121.9 (5)	C8—C9—C10	118.2 (5)
N1—C1—H1	119.0	C8—C9—H9	120.9
C2—C1—H1	119.0	C10—C9—H9	120.9
C3—C2—C1	119.3 (5)	N2—C10—C9	120.9 (5)
C3—C2—H2	120.3	N2—C10—C11	117.1 (5)
C1—C2—H2	120.3	C9—C10—C11	122.1 (5)
C2—C3—C4	120.1 (5)	C10—C11—H11A	109.5
C2—C3—H3	120.0	C10—C11—H11B	109.5
C4—C3—H3	120.0	H11A—C11—H11B	109.5
C3—C4—C5	118.5 (5)	C10—C11—H11C	109.5
C3—C4—H4	120.7	H11A—C11—H11C	109.5
C5—C4—H4	120.7	H11B—C11—H11C	109.5

N2—Zn1—N1—C5	−6.9 (3)	C6—C5—N1—Zn1	7.2 (5)
Cl2—Zn1—N1—C5	−122.7 (3)	C6—C5—N1—C1	−176.3 (4)
Cl1—Zn1—N1—C5	100.0 (3)	N1—C5—C6—N2	−2.7 (5)
N2—Zn1—N1—C1	176.9 (4)	C4—C5—C6—N2	179.1 (4)
Cl2—Zn1—N1—C1	61.1 (4)	N1—C5—C6—C7	176.6 (4)
Cl1—Zn1—N1—C1	−76.2 (4)	C4—C5—C6—C7	−1.6 (7)
Cl1—Zn1—N2—C10	73.8 (4)	C5—C6—N2—Zn1	−3.3 (4)
Cl2—Zn1—N2—C10	−61.8 (4)	C5—C6—N2—C10	179.1 (4)
N1—Zn1—N2—C10	−177.1 (4)	C7—C6—N2—Zn1	177.4 (3)
Cl1—Zn1—N2—C6	−103.7 (3)	C7—C6—N2—C10	−0.2 (6)
Cl2—Zn1—N2—C6	120.7 (3)	N2—C6—C7—C8	1.2 (7)
N1—Zn1—N2—C6	5.4 (3)	C5—C6—C7—C8	−178.1 (4)
C2—C1—N1—C5	−1.2 (7)	C6—C7—C8—C9	−1.2 (8)
C2—C1—N1—Zn1	174.8 (4)	C7—C8—C9—C10	0.3 (8)
N1—C1—C2—C3	−0.2 (9)	C8—C9—C10—N2	0.7 (8)
C1—C2—C3—C4	0.8 (9)	C8—C9—C10—C11	−179.4 (6)
C2—C3—C4—C5	0.0 (8)	C9—C10—N2—Zn1	−178.0 (4)
C3—C4—C5—N1	−1.4 (7)	C9—C10—N2—C6	−0.7 (7)
C3—C4—C5—C6	176.7 (4)	C11—C10—N2—Zn1	2.0 (6)
C4—C5—N1—Zn1	−174.5 (3)	C11—C10—N2—C6	179.3 (5)
C4—C5—N1—C1	2.0 (6)

Zn1—N1	2.066 (4)
Zn1—N2	2.053 (4)
Zn1—Cl1	2.2236 (15)
Zn1—Cl2	2.1995 (13)

N1—Zn1—Cl1	111.08 (11)
N2—Zn1—Cl1	109.16 (11)
Cl2—Zn1—Cl1	116.72 (5)
N1—Zn1—Cl2	116.84 (11)
N2—Zn1—Cl2	117.28 (10)
N2—Zn1—N1	80.31 (15)

6 in total

1. A short history of SHELX.

Authors: George M Sheldrick
Journal: Acta Crystallogr A Date: 2007-12-21 Impact factor: 2.290

2. The crystal structure of di-imidazole-zinc (II) dichloride.

Authors: B K Lundberg
Journal: Acta Crystallogr Date: 1966-12-10

3. Blue phosphorescent Zn(II) and orange phosphorescent Pt(II) complexes of 4,4'-diphenyl-6,6'-dimethyl-2,2'-bipyrimidine.

Authors: Qin-De Liu; Ruiyao Wang; Suning Wang
Journal: Dalton Trans Date: 2004-06-09 Impact factor: 4.390

4. catena-Poly[[(5,5'-dimethyl- 2,2'-bipyridine-κN,N')cadmium(II)]-di-μ-chlorido].

Authors: Roya Ahmadi; Aida Khalighi; Khadijeh Kalateh; Vahid Amani; Hamid Reza Khavasi
Journal: Acta Crystallogr Sect E Struct Rep Online Date: 2008-09-06

5. Dichlorido(5,5'-dimethyl-2,2'-bipyridine-κN,N')zinc(II).

Authors: Aida Khalighi; Roya Ahmadi; Vahid Amani; Hamid Reza Khavasi
Journal: Acta Crystallogr Sect E Struct Rep Online Date: 2008-08-30

6. (4,4'-Dimethyl-2,2'-bipyridine-κN,N')diiodidomercury(II).

Authors: Mohammad Yousefi; Nasim Tadayon Pour; Vahid Amani; Hamid Reza Khavasi
Journal: Acta Crystallogr Sect E Struct Rep Online Date: 2008-09-13

6 in total

16 in total

1. Di-μ-bromido-bis-[bromido(4,4'-dimethyl-2,2'-bipyridine-κN,N')mercury(II)].

Authors: Khadijeh Kalateh; Amin Ebadi; Roya Ahmadi; Vahid Amani; Hamid Reza Khavasi
Journal: Acta Crystallogr Sect E Struct Rep Online Date: 2008-10-15

2. Trichlorido(4,4'-dimethyl-2,2'-bipyridine-κN,N')(dimethyl sulfoxide-κO)indium(III).

Authors: Roya Ahmadi; Khadijeh Kalateh; Anita Abedi; Vahid Amani; Hamid Reza Khavasi
Journal: Acta Crystallogr Sect E Struct Rep Online Date: 2008-09-20

3. Trichlorido(5,5'-dimethyl-2,2'-bipyridine-κN,N')(methanol-κO)indium(III).

Authors: Khadijeh Kalateh; Roya Ahmadi; Amin Ebadi; Vahid Amani; Hamid Reza Khavasi
Journal: Acta Crystallogr Sect E Struct Rep Online Date: 2008-10-04

4. Tetra-kis(6-methyl-2,2'-bipyridine)-1κN,N';2κN,N';3κN,N';4κN,N'-tetra-μ-nitrato-1:2κO:O';2:3κO:O',O'';2:3κO,O':O'';3:4κO:O'-tetra-nitrato-1κO,O';4κO,O'-tetra-lead(II).

Authors: Roya Ahmadi; Khadijeh Kalateh; Robabeh Alizadeh; Zeinab Khoshtarkib; Vahid Amani
Journal: Acta Crystallogr Sect E Struct Rep Online Date: 2009-09-05